Head Of Sales

Head of Sales


Philadelphia, PA


Title evolves to Chief Revenue Officer as the company scales.

About the Client


The company builds an AI-powered estimating and proposal platform for specialty construction contractors. Its software-plus-services offering pulls scope out of RFPs, manages RFIs, and generates proposals so estimators stop missing deadlines and start winning the work they actually want.


The business is an early-revenue, growth-stage company. Backed by leading early-stage investors and headquartered in Philadelphia.

About the Role


The company has product-market fit, real customers, and an industry-baked-in top of funnel via independent reps. What they don't yet have is a fully built sales motion. The founder is currently the primary closer.


The organization is preparing to hire ten Account Executives across the country, each a glazing-industry veteran selling to specialty contractors they've known for decades. The company now needs a leader who can build the system that allows those AEs to succeed at scale.

Responsibilities

• Build the sales motion from scratch. CRM stand-up, sequencing, commission design (including writing the commission spreadsheet yourself), segmentation, ICP, and the closing playbook
• Manage and coach a national team of 10 industry-veteran AEs. These are not classic SaaS reps. They are people who have been selling to contractors for 25 years and need a leader who respects that and still raises the bar
• Translate ethos and pathos selling into a repeatable, gap-selling playbook. Train AEs to move from "the client likes you" to "the client buys because we've quantified the gap"
• Step in to close on the largest enterprise opportunities where industry-veteran AEs may need a more strategic partner across the table. This is not the day job; the day job is building the team and the system
• Partner with the founder on customer-profile work, segmentation, and territory design
• Own the number. Drive the company's next phase of revenue growth
• Report directly to the CEO
• Grow into a CRO-level leadership role as the company scales

Requirements

Must-Haves

• 7 to 12 years in sales, with at least three years leading a quota-carrying team
• A track record of building or rebuilding the sales motion at an early- to growth-stage company - not just optimizing one that already worked
• Software-to-trades experience. You've sold SaaS into blue-collar buyers (specialty contractors, home services, pest control, alarm, construction-tech, field-service). You understand that selling to a glazing GC president is not the same as selling to a CIO
• Strong data fluency paired with operational execution. You don't write decks; you write commission plans, dashboards, and call scripts
• The type of executive presence that earns respect from a 30-year industry veteran on day one
• Comfortable in a founder-led, in-person, build-it-yourself environment

Nice-to-Haves

• Construction, AEC, glazing, curtain wall, or architectural metals exposure
• Veteran or prior service background
• Direct experience hiring, ramping, and managing geographically dispersed AEs

Compensation & Benefits

• Base Salary: $150K-$160K
• OTE: $300K+ with uncapped commission and accelerators
• Equity: meaningful nominal grant
• Compensation above the stated band is possible for the right candidate

Why This Role


Philadelphia preferred.


Open to NYC-based candidates who can travel to Philadelphia two days per week.


Travel for this role is limited. The focus is on managing and enabling the people in front of customers, rather than being the primary field seller yourself.